A GENERAL-METHOD FOR THE PREPARATION OF BENZYLIC ALPHA,ALPHA-DIFLUOROPHOSPHONIC ACIDS - NONHYDROLYZABLE MIMETICS OF PHOSPHOTYROSINE

被引：124

作者：

SMYTH, MS ^{[1
]}

FORD, H ^{[1
]}

BURKE, TR ^{[1
]}

机构：

[1] NCI, DIV CANC TREATMENT, DEV THERAPEUT PROGRAM, MED CHEM LAB, BETHESDA, MD 20892 USA

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(00)74672-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methodology is presented for the preparation of heretofore unreported benzylic alpha,alpha-difluorophosphonic acids. Oxidation of benzylic alpha-hydroxyphosphonates using MnO2 provided a new route for the synthesis of benzylic alpha-oxophosphonate, which were then fluorinated using DAST. Hydrolysis of ester protecting groups yielded alpha,alpha-difluorophosphonic acids. These represent non-hydrolyzable mimetics of arylphosphates which could be of value in the study of cellular phosphotyrosine-utilizing signal transduction pathways.

引用

页码：4137 / 4140

页数：4

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